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Catalytic Arylation Methods: From the Academic Lab to Industrial Processes

ISBN: 978-3-527-33518-3
528 pages
February 2015
Catalytic Arylation Methods: From the Academic Lab to Industrial Processes (3527335188) cover image


This "hands-on" approach to the topic of arylation consolidates the body of key research over the last ten years (and up to around 2014) on various catalytic methods which involve an arylation process. Clearly structured, the chapters in this one-stop resource are arranged according to the reaction type, and focus on novel, efficient and sustainable processes, rather than the well-known and established cross-coupling methods. The entire contents are written by two authors with academic and industrial expertise to ensure consistent coverage of the latest developments in the field, as well as industrial applications, such as C-H activation, iron and gold-catalyzed coupling reactions, cycloadditions or novel methodologies using arylboron reagents. A cross-section of relevant tried-and-tested experimental protocols is included at the end of each chapter for putting into immediate practice, along with patent literature.
Due to its emphasis on efficient, "green" methods and industrial applications of the products concerned, this interdisciplinary text will be essential reading for synthetic chemists in both academia and industry, especially in medicinal and process chemistry.
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Table of Contents

Preface XV

List of Abbreviations XVII

1 Cross-Coupling Arylations: Precedents and Rapid Historical Review of the Field 1

1.1 Metal-Catalyzed Cross-Couplings: From Its Origins to the Nobel Prize and Beyond 1

1.2 Arylation:What Is So Special? 12

1.3 Recent New Developments 14

1.4 Selected Experiments from the Literature 85

2 Amine, Phenol, Alcohol, and Thiol Arylation 95

2.1 Introduction 95

2.2 Pd-Catalyzed Processes 98

2.3 Cu-Catalyzed and Promoted Arylations: (CAr–N Bond Formation) 118

2.4 Fe-Catalyzed Arylations 134

2.5 Ni-Catalyzed Reactions 137

2.6 Co-Catalyzed Arylations 139

2.7 Mn-Catalyzed Arylations 140

2.8 Cd-Catalyzed Arylations 140

2.9 Bi(III) and Indium Oxide-Catalyzed Thiol Arylations 141

2.10 Conclusions and Final Comment 141

2.11 Selected Experiments from the Literature 141

3 Decarboxylative Coupling Techniques 151

3.1 Introduction 151

3.2 Pd-Catalyzed Versions 152

3.3 Other Metal-Catalyzed Versions 163

3.4 Conclusions 166

3.5 Selected Experiments 169

4 C–H Bond Activation for Arylations 173

4.1 Introduction 173

4.2 C(sp2)–H Activations 176

4.3 Conclusions 240

4.4 Selected Experiments from the Literature 240

5 Conjugate Additions 247

5.1 Conjugate Additions: A Powerful Tool for Appending Organic Residues to Cyclic and Acyclic Substrates 247

5.2 Applications of Rh Catalysts 248

5.3 Applications of Pd Catalysts 270

5.4 Applications of Ru and Other Catalysts 279

5.5 Conclusions 286

5.6 Selected Experiments 287

6 Imine Arylations–Synthesis of Arylamines 292

6.1 Arylation of C=N Bonds: Simple Access to Chiral Amine Units 292

6.2 Application of Rh Catalysts 292

6.3 Application of Pd Catalysts 305

6.4 Application of Ru and Other Catalysts 313

6.5 The Petasis–Akritopoulou Reaction 315

6.6 Conclusions 322

6.7 Selected Experiments 324

7 Carbonyl Group Arylation 329

7.1 Introduction 329

7.2 Application of Rh Catalysts 329

7.3 Application of Pd Catalysts 349

7.4 Application of Ru and Other Catalysts 355

7.5 Conclusions 370

7.6 Selected Experiments 370

8 α-Arylation Processes 376

8.1 Introduction 376

8.2 Arylation of Enolates and Equivalents 377

8.3 Other Metal-Catalyzed α-Arylations 419

8.4 Conclusions 427

8.5 Selected Experiments 428

9 Catalytic Cycloaddition Aromatization Processes 436

9.1 Introduction 436

9.2 Cycloaddition Events 436

9.3 Radical-Based Cycloaromatization Processes 474

9.4 Conclusions 482

9.5 Selected Experiments from the Literature 482

References 486

Index 491

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Author Information

Anthony J. Burke obtained a BSc (joint honours in Chemistry & Biology, 1988) from NUI-Maynooth and a PhD from University College Dublin, Ireland (1993, under the supervision of W. Ivo O'Sullivan, in the group of Prof. DMX Donnelly). After post-doctoral studies with Steve Davies (Oxford, 1993-96) and Chris Maycock (ITQB -- Portugal, 1996-1999) he obtained a position as assistant professor in organic chemistry, at the University of Evora, Portugal. His interests lie mainly in the areas of asymmetric synthesis and catalysis, reaction mechanisms and medicinal chemistry. In 2012 he obtained his aggregation in organic chemistry from the University of Évora. He is a former vice-president of the organic chemistry division of the Portuguese Chemical Society, and has journal editorial experience. Professor Burke has authored over 60 publications, including a book chapter, papers and patents. He founded Chiratecnics Lda -- a chiral technology specialist house in 2009.

Carolina S. Marques was born in Alcobaça (Portugal) in 1981. She finished her first degree in chemistry at the University of Évora, Portugal in 2005 and obtained a masters' degree in Applied Chemistry at the same institution in 2007. In 2008 she won a scholarship to work with Prof. Carlos Afonso at Instituto Superior Técnico, Portugal. In 2009 she returned to Évora, after winning a national PhD scholarship to do research in the field of asymmetric catalysis under the supervision of Prof. Burke, which she defended successfully in 2013. Dr Marques is currently developing new catalytic methods using metal based catalysts for the synthesis of small-molecules for neurodegenerative diseases. She was the recipient of the prize of best PhD in organic chemistry by the SPQ in 2013 and has authored 25 publications, including patents.

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“Those working in either industry or academia will find this book a valuable resource to turn to.”  (Chemistry World, 1 March 2015)

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